반응 #7944

반응 방정식

2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone

acetic acid

pyrrolidine

→

9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

수율 55.5%

용매

toluene

Et2O

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   세척washed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL)
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   기타evaporated under vacuum to a dark brown oil (0.86 g)
6. 6
   기타The crude product was purified by chromatography on a Biotage FLASH 40S column
7. 7
   세척eluting with 9:1 hexanes-EtOAc

실험 절차

A solution of impure 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone (0.96 g, 3.17 mmol), acetic acid (0.182 mL, 3.18 mmol) and pyrrolidine (0.265 mL, 3.18 mmol) in anhydrous toluene (15.9 mL) was stirred and heated in an oil bath at 80° C. for 16 hours. After cooling, the reaction mixture was diluted with Et2O (100 mL), washed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to a dark brown oil (0.86 g). The crude product was purified by chromatography on a Biotage FLASH 40S column, eluting with 9:1 hexanes-EtOAc, to afford 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.50 g) as an off-white solid.

출처